Antifungals

Lipids of Pathogenic Fungi

Volumn , Issue , 2017, Pages 235-252

  Ibrahim, A S ^a   Prasad, R ^b   Ghannoum, M A ^c  

^a HARBOR UCLA MEDICAL CENTER   (United States)

^b JAWAHARLAL NEHRU UNIVERSITY   (India)

^c CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345556127     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9780203711521     Document Type: Chapter

References (78)

1. Borgers, M., Mechanism of action of antifungal drugs with special reference to the imidazole derivatives, Rev. Infect. Dis., 2, 520, 1980.
2. Gravestock, M.B. and Riley, J., Antifungal chemotherapy, Ann. Rev. Med. Chem., 19, 127, 1984.
3. Kerridge, D., The plasma membrane of Candida albicans and its role in the action of antifungal drugs, in The Eukaryotic Microbial Cell, Gooday, G.W., Lloyd, D. and Trinci, A.P.J., Eds., Cambridge University Press, Cambridge, 103, 1980.
4. Medoff, G., Brajtburg, J., Kobayashi, G.S. and Bolard, J., Antifungal agents useful in therapy of systemic infections, Ann. Rev. Pharmacol. Toxicol., 23, 303, 1983.
5. Marriott, M.S., Isolation and chemical characterization of plasma membranes from the yeast and mycelial forms of Candida albicans, J. Gen. Microbiol., 86, 115, 1975.
6. Sundaram, S., Sullivan, P.A. and Shepherd, M.G., Changes in lipid composition during starvation and germ tube formation in Candida albicans, Exp. Mycol., 5, 140, 1981.
7. Ghannoum, M.A., Janini, G., Khamis, L. and Radwan, S.S., Dimorphism-associated variations in the lipid composition of Candida albicans, J. Gen. Microbiol., 132, 2367, 1986.
8. Pierce, A.M., Pierce, H.D., Jr., Unrau, A.M. and Oehlschlager, A.C., Lipid composition and polyene antibiotic resistance of Candida albicans mutants, Can. J. Biochem., 56, 135, 1978.
9. Marriott, M.S., Inhibition of sterol biosynthesis in Candida albicans by imidazole-containing antifungals, J. Gen. Microbiol., 117, 253, 1980.
10. Taylor, F.R., Rodriguez, R.J. and Parks, L.W., Relationship between antifungal activity and inhibition of sterol biosynthesis in miconazole, clotrimazole and 15-azasterol, Antimicrob. Agents Chemother., 23, 515, 1983.
11. Medoff, G. and Kobayashi, G.A., The polyenes, in Antifungals Chemotherapy, Speller, D.C.E., Ed., John Wiley & Sons, London, 1980, chap. 3.
12. Kinsky, S.C., The effect of polyene antibiotic on permeability in Neurospora crassa, Biochem. Biophys. Res. Commun., 4, 353, 1961.
13. Kinsky, S.C., Alterations in the permeability of Neurospora crassa due to polyene antibiotics, J. Bacteriol., 82, 889, 1961.
14. Kobayashi, G.S. and Medoff, G., Antifungal agents: recent developments, Ann. Rev. Microbiol., 31, 291, 1977.
15. Hurley, R., deLoouvois, J., and Mulhall, A., Yeasts as human and animal pathogens, in The Yeast, Vol. 1, 2nd ed., Rose, A.H. and Harrison, J.S., Eds., Academic Press, London, 207, 1987.
16. Norman, A.W., Demel, R.A., de Kruijff, B., Guerts-van Kessel, W.S.M. and Van Deenen, L.L.M., Studies on the biological properties of polyene antibiotics: comparison of other polyenes with filipin in their ability to interact specifically with sterol, Biochim. Biophys. Acta, 290, 1, 1972.
17. Feingold, D.S., The action of amphotericin B on Mycoplasma laidlawaii, Biochem. Biophys. Res. Commuti., 19, 261, 1965.
18. Weber, M.M. and Kinsky, S.C., Effect of cholesterol on the sensitivity of Mycoplasma laidlawaii to the polyene antibiotic filipin, J. Bacteriol., 89, 306, 1965.
19. Gottleib, D.H., Carter, H.E., Sloneker, J.G. and Immann, A., Protection of fungi against polyene antibiotics by sterols, Science, 128, 361, 1958.
20. Lampen, J.O., Arnow, P.M. and Saferman, R.S., Mechanism of protection by sterol against polyene antibiotics, J. Bacteriol., 80, 200, 1960.
21. Zygmunt, W.A. and Tavorminu, P.A., Steroid interference with antifungal activity of polyene antibiotics, App. Microbiol., 14, 865, 1966.
22. Iannitelli, R.C. and Ikawa, M., Effect of fatty acids on action of polyene antibiotics, Antimicrob. Agents Chemother., 17, 861, 1980.
23. Norman, A.W., Demel, R.A., de Kruijff, B. and Van Deenen, L.L.M., Studies on the biological properties of polyene antibiotics. Evidence for the direct interaction of filipin with cholesterol, J. Biol. Chem., 247, 1918, 1972.
24. Kleinschmidt, M.G., Chough, K.S. and Mudd, J.B., Effect of filipin on liposomes prepared with different types of steroids, Plant Physiol, 49, 852, 1972.
25. Schroeder, F., Holland, J.F. and Bieber, L.L., Fluorimetrie evidence for the binding of cholesterol to the filipin complex, J. Antibiot., 24, 846, 1971.
26. Verklelij, A., de Kruijff, B., Gerritsen, W.F., Demel, R.A., Van Deenen, L.L.M. and Ververgart, P., Freeze-etch electron microscopy of erythrocytes, Acholeplasma laidlawaii cells and liposomal membranes after the action of filipin and amphotericin B, Biochim. Biophys. Acta, 291, 577, 1973.
27. de Kruijff, B. and Demel, R.A., Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawaii cells and lecithin liposomes. III. Molecular structure of the polyene antibiotic-cholesterol, Biochim. Biophys. Acta, 339, 57, 1974.
28. Tillack, T.W. and Kinsky, S.C., A freeze-etch study of the effect of filipin on liposomes and human erythrocyte membranes, Biochim. Biophys. Acta, 323, 43, 1973.
29. Holz, R.W., The effects of the polyene antibiotics nystatin and amphotericin B on the thin lipid membranes, Ann. N. Y. Acad Sci., 235, 469, 1974.
30. Kerridge, D., The protoplast membrane and antifungal drugs, in Fungal Protoplasts, Applications in Biochemistry and Genetics, Peberdy, J.F. and Ferenczy, L., Eds., Marcel Dekker, New York, 135, 1985.
31. Vanden Bossche, H., Willemsens, G., Cools, W., Marichal, P. and Lauwers, W., Hypothesis on molecular basis of the antifungal activity of P-substituted imidazoles and triazoles, Biochem. Soc. Trans., U.K., 11,665, 1983.
32. Rao, T.V.G., Das, S. and Prasad, R., Effect of phospholipid enrichment on nystatin action: differences in antibiotic sensitivity between in vivo and in vitro conditions, Microbios, 42, 145, 1985.
33. Rao, T.V.G., Trivedi, A. and Prasad, R., Phospholipid enrichment of Saccharomyces cerevisiae and its effect on polyene sensitivity, Can. J. Microbiol., 31, 322, 1985.
34. Hsu Chen, C.C. and Feingold, D.S., Polyene antibiotic action on lecithin liposomes: effect of cholesterol and fatty acyl chains, Biochem. Biophys. Res. Commun., 51, 972, 1973.
35. Sokol-Anderson, M.L., Brajtburg, J. and Medoff, G., Amphotericin B-induced oxidative damage and killing of Candida albicans, J. Infect. Dis., 154, 76, 1986.
36. Sokol-Anderson, M.L., Brajtburg, J. and Medoff, G., Sensitivity of Candida albicans to amphotericin B administered as single or fractionated doses, Antimicrob. Agents Chemother., 29, 701, 1986.
37. Holt, R.J., The imidazoles, in Antifungal Chemotherapy, Speller, D.C.E., Ed., John Wiley & Sons, Chichester, England, 107, 1980.
38. Van Cutsem, J.M. and Thienpont, D., A broad spectrum antimycotic agent with antibacterial activity, Chemotherapy, 17, 392, 1972.
39. Iwata, K., Yamaguchi, H. and Hirantani, T., The mode of action of clotrimazole, Sabouraudia, 11, 158, 1973.
40. Iwata, K., Kanda, Y., Yamaguchi, H. and Oumi, M., Electronmicroscopic studies on the mechanism of action of clotrimazole on Candida albicans, Sabouraudia, 11, 205, 1973.
41. Swamy, K.H.S., Sirsi, M. and Rao, G.R., Studies on the mechanism of action of miconazole: effect of miconazole on respiration and cell permeability of Candida albicans, Antimicrob. Agents Chemother., 5, 420, 1974.
42. Vanden Bossche, H., Biochemical effects of miconazole on fungi. I. Effects on the uptake and/or utilization of purines, pyrimidines, nucleosides, amino acids and glucose by Candida albicans, Biochem. Pharmacol., 23, 887, 1974.
43. Vanden Bossche, H., Willemsens, G., Cools, W., Lauwers, W.F.J. and Lejeune, L., Biochemical effect of miconazole on fungi. II. Inhibition of ergosterol biosynthesis in Candida albicans, Chem. Biol. Interact., 21, 59, 1978.
44. Berg, D. and Plempel, M., Bifonazole, a biochemist’s view, Dermatologia, 169, 3, 1984.
45. Koh, T.Y., Marriott, M.S., Taylor, J. and Gale, E.F., Growth characteristics and polyene sensitivity of a fatty acid auxotroph of Candida albicans, Antimicrob. Agents Chemother., 102, 105, 1977.
46. Hitchcock, C.A., Dickinson, K., Brown, S.B., Evands, E.G. and Adams, D.J., Interaction of azole antifungal antibiotics with cytochrome P450-dependent 14a-sterol demethylase purified from Candida albicans, J. Biochem., 266, 475, 1990.
47. Vanden Bossche, H. and Willemsens, G., Effect of the antimycotics, miconazole and ketoconazole on cytochrome P450 in yeast microsomes and rat liver microsomes, Arch. Int. Physiol. Biochem., 90, B218, 1982.
48. Yamaguchi, H., Antagonistic action of lipid components of membranes from Candida albicans and various other lipids on two imidazole antimycotics, clotrimazole and miconazole, Antimicrob. Agents Chemother., 12, 16, 1977.
49. Vanden Bossche, H., Ruyschaert, J.M., Defrise-Quertain, F., Willemsens, G., Cornelissen, F., Marichal, P., Cools, W. and Van Cutsem, J., The interaction of miconazole and ketoconazole with lipids, Biochem. Pharmacol., 31, 2609, 1982.
50. Portillo, F. and Gancedo, C., Model of action of miconazole on yeast:inhibition of mitochondrial ATPase, Eur. J. Biochem., 143, 273, 1984.
51. Surarit, R. and Shepherd, M.G., The effect of azole and polyene antifungals on the plasma membrane enzymes of Candida albicans, J. Med. Vet. Mycol., 25, 403, 1987.
52. Ghannoum, M.A., Spellberg, B.J., Ibrahim, A.S., Ritchie, J.A., Currie, B., Spitzer, E., Edwards, J.E., Jr. and Casadevall, A., Sterol composition of Cryptococcus neoformans in the presence and absence of fluconazole, Antimicrob. Agents Chemother., 38, 2029, 1994.
53. Vanden Bossche, H., Heeres, J., Backx, L., Marichal, P. and Willemsens, G., Discovery, chemistry, mode of action and selectivity of itraconazole, in Cutaneous Antifungal Agents, Rippon, J.W. and Fromtling, R.A., Eds., Marcel Dekker, Inc., New York, 263,1993.
54. Vanden Bossche, H., Marichal, P., Gorrens, J., Bellens, D., Coene, M.C., Lauwers, W., Le Jeune, L., Moereels, H. and Janssen, P.A.J., Mode of action of antifungals of use in immunocompromised patients. Focus on Candida glabrata and Histoplasma capsulatum, in Mycoses in AIDS Patients, Vanden Bossche, H., Mackenzie, D.W.R., Cauwenbergh, G., Van Cutsem, J., Drouhet, E. and Dupont, B., Eds., Plenum Press, New York, 223,1990.
55. Vanden Bossche, H., Marichal, P., Gorrens, J., Coene, M.C., Willemsens, G., Bellens, D., Roels, I., Moereels, H. and Janssen P.A.J., Biochemical approaches to selective antifungal activity. Focus on azole antifungals, Mycoses, 32 (Suppl. 1), 35,1989.
56. Vanden Bossche, H., Marichal, P., Gorrens, J., Geerts, H. and Janssen, P.A.J., Mode of action studies. Basis for the search of new antifungal drugs, Ann. N. Y. Acad. Sci., 544, 191, 1988.
57. Nozawa, Y. and Morita, T., Molecular mechanisms of antifungal agents associated with membrane ergosterol. Dysfunction of membrane ergosterol and inhibition of ergosterol biosynthesis, in In vitro and in vivo Evaluation of Antifungal Agents, Iwata, K. and Vanden Bossche, H., Eds., Elsevier Science Publishers, B.V. Amsterdam, 111, 1986.
58. Ganzinger, U., Stephen, A. and Gumhold, G., Treatment of dermatophytosis with nafitifine: a new topical antifungal agent, Clin. Trials J., 19, 342, 1982.
59. Georgopoulos, A., Petranyi, G., Mieth, H. and Drews, J., In vitro activity of nafitifine, a new antifungal agent, Antimicrob. Agents Chemother., 19, 386, 1981.
60. Ryder, N.S., Seidl, G., and Troke, P., Effect of the antimycotic drug nafitifine on growth of and sterol biosynthesis in Candida albicans, Antimicrob. Agents Chemother., 25, 483, 1984.
61. Ryder, N.S., 15th FEBS Meeting, Brussels, Belgium, Abstr. No. 083, 1983.
62. Morita, T. and Nozawa, Y., Effects of antifungal agents on ergosterol biosynthesis in Candida albicans and Trichophyton mentagrophytes:differential inhibitory sites of naphthiomate and miconazole, J. Invest. Dermatol., 85, 434, 1985.
63. Georgopapadakou, N.H., Dix, B.A., Smith, S.A., Freundenberger, J. and Funke, P.T., Effects of antifungal agents on lipid biosynthesis and membrane integrity in Candida albicans, Antimicrob. Agents Chemother., 31,46, 1987.
64. Nomura, S., Horiuchi, T., Omura S. and Hata, T., The action mechanism of cerulenin. I. Effects of cerulenin on sterol and fatty acid biosynthesis in yeast, J. Biochem., 71, 783, 1972.
65. Kawaguchi, A., Tomoda, H., Nozoe, S., Omura S. and Okuda, S., Mechanism of action of cerulenin on fatty acid synthase: effect of cerulenin on iodoacetamide-induced malonyl CoA decarboxylase activity, J. Biochem., 92, 7, 1982.
66. Ohno, T., Kesado, T., Awaya, J. and Omura S., Target of inhibition by the anti-lipogenic antibiotic cerulenin on sterol synthesis in yeast, Biochem. Biophys. Res. Commun., 57, 1119, 1974.
67. Sanadi, S., Pandey, R. and Lullez, G.K., Reversal of cerulenininduced inhibition of phospholipids, and sterol synthesis by exogenous fatty acid/sterols in Epidermatophyton floccosum, Biochim. Biophys. Acta, 921,341, 1987.
68. Mago, N. and Khuller, G.K., Influence of lipid composition on the sensitivity of Candida albicans to antifungal agents, Ind. J. Biochem. Biophys., 26, 30, 1989.
69. Lehrer, N., Segal, E., Cihlar, R.L. and Calderone, R.A., Pathogenicity of vaginal candidiasis: studies with a mutant which has reduced ability to adhere in vitro, J. Med. Vet. Mycol, 24, 127, 1986.
70. Calderone, R.A., Cihlar, R.L., Lee, D., Hoberg, K. and Scheld, W.M., Yeast adhesion in the pathogenesis of Candida albicans endocarditis: studies with adherence negative mutants, J. Infect. Dis., 154,710, 1985.
71. Ghannoum, M.A., Abu Elteen, K., Ellabib, M. and Whittaker P.A., Antimycotic effects of octenidine and pirtenidine, J. Antimicrob. Chemother., 25, 237, 1990.
72. Sedlock, D.M. and Bailey, D.M., Microbicidal activity of octenidine hydrochloride, a new alkanediylbis (pyridine) germicidal agent, Antimicrob. Agents Chemother., 28, 786, 1985.
73. Fryberg, M., Oehlschlager, A.C. and Unrau, A.M., Sterol biosynthesis in antibiotic resistant yeast strains, Arch. Biochem. Biophys., 160, 83, 1974.
74. Weete, J.D., Lipid Biochemistry of Fungi and Other Organisms, Plenum Press, New York, 1980.
75. 1st World Congress on Health Significance of Garlic and Garlic Constituents, Washington, D.C., August, 1990.
76. Barone, F.E. and Tansey, M.R., Inhibition of growth of zoopathogenic fungi by garlic extract, Mycologia, 61, 882, 1975.
77. Adetumbi, M., Javor, G.T. and Lau, B.H.S., Allium sativum (garlic) inhibits lipid biosynthesis in Candida albicans, Antimicrob. Agents Chemother., 30, 499, 1986.
78. Ghannoum, M.A., Studies on the anticandidal mode of action of Allium sativum (garlic), J. Gen. Microbiol., 134, 2917, 1988.